What is the most interesting question you can ask to get to know someone?
Last Updated: 23.06.2025 04:19
21- What's your favorite way to spend a weekend or time off?
6- Do you have dreams? Can you remember them? What do you usually dream about?
What would you say to prove to yourself that it was really you?
Who is the beast of Revelation 13?
Can you Deep Throat? Do you like the taste of yourself?
39~ What are your love languages?
If you win, what will you make them do?
7- What are your thoughts on religion? Is there an afterlife?
7- What if a person smells a certain way? 8- How about smoking?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Why has my ex moved on so fast after years of being together with me?
What is your view on sex? Meaning, When/Where/ How often/
Any that are a turn off?
Family Relation Age Play
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Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
34~ Do you like the lights on or off during sex?
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4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
* Give a rating for each one (0-100)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
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If you say it, I will stop, and we can talk about it when you are ready.
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
14- Do you have a “Deal Breaker”, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
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80~ Share your top three fantasies/desires. (Be detailed) 😊
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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What have you learned about me that was new and/or surprising?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
37- Do you like your name? If you could change it, what would you change it too?
If NO, would you ever have one? Would it be with 2 men or 2 women?
85~ If I gave you a “Free Pass” for you to do anything to me for one hour, knowing that no matter what you did,
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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48~ Have you ever paid or been paid for sex?
9- What’s your favorite season and why? What’s your least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
How old are you? Male or Female?
If YES, was it with 2 men or 2 women? Did you enjoy it?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Do you like it when they show and tell you what they want?
Get this wrong and this could mean the end… :-) some funny, some not…
60~ How important is oral sex? Do you like receiving? Do you like giving?
71~ Would you give your partner a hand or foot job? Would you receive one?
19- Do/have you smoked? What do you prefer? How often?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
3- What Superhero or Superpower would you want to be/have?
4- For a pet, Cat, dog or other?
81~ Do you have any kinks and/or fetishes?
70~ Would/do you have/like anal sex?
51~ What tends to bring a smile to your face?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
How about if they talk dirty and/or call you names?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
21~ What was the best date you ever went on? What has been the worst?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
8- What are your thoughts on politics?
What is your favorite toy? Ever wanted to try a specific toy?
Please share Did you stop?
10~ How many dates are necessary before you to have sex with someone?
13- How about having a certain hair cut/style?
11- List at least 5 things on your bucket list. Have you done any of them already?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
13- What’s your favorite drink? What’s your least favorite?
Would you mind if your partner watched it? How about together vs alone?
36~ What is your favorite time of day to have sex/make love?
10- What is your favorite family tradition? What’s your least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Do you watch it? What is your favorite?
Do you think this brought you closer together?
You know that I will be 100% truthful, so ask.
A comprehensive questionnaire, this should be a fun exercise to get to know each other. Try to give as much detail as possible when answering questions. You can go through this together and talk about each question or fill out the questionnaire as completely as you can and once you are done, go through each question together. If you have been together for a while, it is also fun to try to answer the questions for your partner. Remember this should be fun, so if you do not wish to answer a question you can “PASS” and not answer. Both should answer honestly and without judgement. (This is important, without judgement) I hope this helps you get closer and strengthens your relationship… You can learn a lot about the other person… and yourself…
40~ If you could go back in time, and relive your life, with the knowledge you have now, what age would you go back to and why?
19~ Who/when was your first “heartbreak”?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
84~ How do you feel about reading/listening to adult stories?
Would you read them together?
49~ How many times have you been married? Why did they end?
9- If you could have three wishes, what would they be? Why?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
42~ What’s your biggest regret in life?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
What do you dislike about me? I asked you to be 100% honest.
45~ How do you feel about me blindfolding you? How about blindfolding me?
2- What’s your favorite color? Do you a least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
22- Do you have any birth marks? How about scars? Care to share how you got them?
52~ Are you willing to make “those types” of bets with your partner?
Over time has your thoughts on sex changed?
27- What was/ is nickname? Does it have a meaning behind it?
15~ Have you ever been “in love”? Who? Care to Share?
85~ If you gave me a “free Pass” to have me do anything for one hour, what would you want me to do to you?
Does the thought excite you? Care to share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
17- What’s your favorite holiday? What’s your least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
What is your favorite position? Why?
14- What is an embarrassing moment in your life? How about your most embarrassing?
29- How superstitious are you?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
44~ Care to share something about yourself that no one else knows about you?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
50~ How many children do you have? What are their ages?
92~ Have you ever had or have an STD? How many? What was it?
29~ What are some things that turn you off? What is your biggest turn off?
*** Deal Breaker Questions ***
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
1- What was your first impression of me? Has it changed?
12- What is the weirdest thing you've ever eaten?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
*** Random Questions ***
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
If yes, what?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
31- If given a chance to be immortal, would you take it? Why?
8- What's your favorite flavor of ice cream? Do you a least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
3- What’s your favorite smell? Do you a least favorite?
32- What's your greatest talent? Can I see it right now?
13~ Is there a difference between, making love, having sex, and fucking?
17- Have you ever done drugs? Which ones? How often?
*** What’s Your Favorite…? ***
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Doctor/Nurse Stripper/Client
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Do you like the “69” position? Do you prefer to be on top or bottom?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Escort/Client Job Applicant/Hiring Manager
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
61~ How willing would you be to try new sexual positions?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
5~ When you first started having sex, was it what you thought it would be?
3- Should Pluto still be considered a planet? 4- How about smoking?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Teacher/Student Stranger/One Night Stand
40~ What’s the weirdest place you’ve ever had sex?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
What was the longest? What was the shortest?
30~ What's something unexpected that turns you on?
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couples’ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETC…)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
28~ What are some things that turn on? What is your biggest turn on?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
Repairman/Lonely Wife Virgin/Experienced
Nothing too Serious
Would you ever want to be woken up with oral and/or intercourse?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Nurse/Patient Celebrity/Fan
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
1- What’s your favorite animal? Do you a least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
75~ If your partner wants an orgasm/have sex when you don't desire to have sex, how do you plan to deal with their needs?
50~ Where would you like to be touched more? Do you have a place that you want to be touched, that no one has, or has only happened a couple times? How about less?
82~ Do you have any fantasies involving Role-Playing?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
7-What do I do in bed that drives you wild? How about, what turns you off?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
38~ Share your most embarrassing sexual memory?
59~ Have/do you masturbate? How often? What do you use? (Toys, Phone sex, Erotica, Hard Core, shower/water, etc) Would you, while your partner watches?
89~ Do you like taking showers together?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Master/Slave Boss/Maid
11- Is there something you would like me to do, in any area of our relationship that I have not done, or you want more of?
41~ What are you best at in bed? What do you think you are not so good at? Anything you want to get good at?
15- What's your favorite saying? What word or phrase is your least favorite?
18~ Who/when was your first “crush”?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
2~ How old were you when you got to 2nd base? (Tongue kissing, breast feeling, or outside the clothes genital contact) Who? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
47~ What would be your dream job and why?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
67~ Do you like it when your partner moans and/or is vocal during sex?
These go from easy to answer, to OMG, you really want to know that?! to some serious thought. Take your time and have fun with this. The past is the past… it got you two here together…
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
53~ How much can you tell me about the one thing you are most passionate about?
Would you do it again, and would you rather 2 females or 2 males?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
23~ What do you believe is required to have a successful and healthy relationship? (This is important, take your time, and really think about this)
Would you allow me to clean every part of your body with my soapy hands and fingers?
10- List 5 of your top pet peeves.
How many times do you think you have “made love”?
Have you ever? Care to Share?
51~ Are you willing to play adult games with your partner?
I would allow you to do it… What would you do to me?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
5- Have you ever been hypnotized? Would you allow yourself to be?
23- What is your dream job? What was it as a child?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
49~ If you could, would you want to be the opposite sex for a day, week, or year?
62~ Have you used adult toys?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
20- What’s your favorite candy? What’s your least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
How well do you know me? And some of your thoughts about me
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
The Ice Breaker Questions
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
28- What are some things that people do that irritate you?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
How many partners have you had oral sex with? Who? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
What have you learned about yourself that you did not before this?
Prisoner/Prison Guard Landlord/Tenant
26~ What side of the bed do you sleep on?
9- Is there something you’ve always wanted to ask me but you’re afraid?
13- What is the craziest/scariest thing you've ever done?
25~ How do you feel about PDA? (Public Display of Affection)
Do you have a favorite? Is it ok if your partner does?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
That one or two things that made you go hmmmm, OMG or wow!
76~ Have you had a threesome? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** Questions about Relationships/Past ***
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
12- What’s your favorite food? What’s your least favorite?
Model/Photographer Police/Criminal
83~ How do you feel about Porn?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
33- Beach or Mountains? Or is there another place to like better?
15- What bad habit do you wish you could quit? Do you have any addictions?
11~ Have you ever been caught by your parents or children or others while having sex?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
52~ What are your hobbies?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Would /have you ever given your partner a lap dance and Striptease?
1~ How old were you when you had your first kiss? Who? Care to Share?
Any that are a turn off?
*** Questions About Me ***
19- What’s your favorite fairytale? What’s your least favorite?
48~ Do you have any siblings? Are you close to your family?